HCID 66698120, compound → HCID 53485979, compound

HRID 516409Notes

Reaction equation

HRID 516409 reaction equation
[CH3:1][NH:2][S:3]([CH:6]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)(=[O:5])=[O:4]>CO.[Pd]>[CH3:1][NH:2][S:3]([CH:6]1[CH2:10][CH2:9][NH:8][CH2:7]1)(=[O:5])=[O:4]

Participants

4

Reactant 1

HCID 66698120HCID 66698120, compound

Product 1

HCID 53485979HCID 53485979, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the above benzyl carbamate (173 mg, 0.580 mmol) and 10% Pd on carbon in MeOH (15 mL) was hydrogenated for 24 hrs. The reaction mixture was filtered through celite, the celite pad was washed with MeOH, and the solvent was removed under vacuum to give N-methyl-3-pyrrolidinesulfonamide (92 mg, 97%) which was used in the next step without further purification. 1H NMR (DMSO-d6) δ 6.89 (br s, 1H), 3.62 (qd, J=8.9, 6.3 Hz, 1H), 2.99 (m, 2H), 2.82 (m, 1H), 2.72 (m, 1H), 2.59 (s, 3H), 1.95 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite pad was washed with MeOH
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-543134cf612a49f3979f199a7003f901
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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